103260-75-9

Upstream product

• 5416-93-3 4-Methoxyphenyl isocyanate 
• 1275575-33-1 C₁₂H₁₅NO₅ 

Downstream Products

• 1355558-42-7 C₁₇H₁₄BrNO₅ 
• 1275574-39-4 5-(3-bromo-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione 
• 1275575-34-2 5-[3-(N,N-dimethylaminomethyl)-4-hydroxybenzylidene]-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione 
• 1275575-54-6 5-(3-carboxy-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione 
• 1296646-55-3 5-(3,5-dichloro-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione 
• 1275574-83-8 5-[(5-hydroxypyridin-2-yl)methylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one 
• 1275574-81-6 5-[(6-bromo-5-hydroxypyridin-2-yl)methylidene]-3-(4-methoxyphenyl)-2-thioxo-1,3-oxazolidin-4-one 
• 1275574-43-0 5-(3-cyano-4-hydroxybenzylidene)-3-(4-methoxyphenyl)-1,3-oxazolidin-2,4-dione 

Relevant academic research and scientific papers

Identification of oxazolidinediones and thiazolidinediones as potent 17β-hydroxysteroid dehydrogenase type 3 inhibitors

Novel and potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) were identified based on oxazolidinedione and thiazolidinedione derivatives, starting from a high-throughput screening hit, 5-(3-bromo-4-hydroxybenzyl)-3-(4-methoxyphenyl)-1

Discovery of potent and orally bioavailable 17β-hydroxysteroid dehydrogenase type 3 inhibitors

We have previously reported the discovery of a new class of potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3) derived from benzylidene oxazolidinedione and thiazolidinedione scaffolds. In this study, these analogs were designed, synthesized, and evaluated in a human cell-based assay. The detailed structure-activity relationship (SAR) surrounding this pharmacophore were developed, and consequently a number of compounds from this series demonstrated single-digit nanomolar 17β-HDS3 inhibitory activity in vitro. Subsequent optimization work in pursuit of the improvement of oral bioavailability demonstrated in vivo proof-of-concept by prodrug strategy based on phosphate esters for these 17β-HSD3 inhibitors. When a phosphate ester 16 was administered orally at a high dose of 100 mg/kg, 16 showed approximately two times more potent testosterone (T)-lowering effect against a positive control in the luteinizing hormone-releasing hormone (LH-RH)-induced T production assay. The T-lowering effect continued at ca 10% level of control over 4 h after administration. The nonsteroidal molecules based on this series have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer.